Medicinal chemistry is increasingly exploiting fluorine atoms. Substitution of a hydroxyl function by a fluorine atom can provide beneficial effects such as an increase of drugs metabolic stability or enable favorable interactions with a target protein.<br/>Carbohydrates bearing a fluorine atom in place of a hydroxyl group have found applications in biochemical investigations as mechanistic probes or to study lectin- carbohydrate interactions. Thus, the rapid synthesis of fluorinated carbohydrates could lead to the discovery of glycomimetic with novel biological activities.<br/>As part of our ongoing program related to the preparation of fluorinated carbohydrates, we investigated the rapid synthesis of various mono- and polyfluorinated glucopyranoses starting from levoglucosan (1,6-anhydro-β-D-glucopyranose). This inexpensive starting material allowed us to use the 1,6-anhydro core to avoid the preliminary protection of the O-6 and anomeric positions and could easily afford scalable fluorinated carbohydrates via simple experimental protocols. Thus, the synthesis of mono-, di-, gendifluoro- or more complexes fluorinated glucose was achieved. This strategy also allowed us to prepare various orthogonally protected fluorinated sugars, useful intermediates for the preparation of complex oligosaccharide derivatives.

Synthesis of fluorinated glucopyranose derivatives from levoglucosan

256th National Meeting (2018)

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